This paper addresses the development of the prison officer occupation within two prison systems, often characterized as “penal welfare” systems, namely the Swedish and the Norwegian. Despite a common origin, the development in the last decades shows diverging tendencies. What are the signs of, and the strategies behind, this development? The paper is based on documents, interviews with key positioned persons in these organizations, and data from a recent research project. Results show that while the Norwegian prison officer training is developed towards a University degree, the Swedish one is shortened to 20 weeks and made more vocational. The Norwegian prison officer training is developing in accordance to a traditional professionalization strategy. The Swedish one is adjusted to security-differentiation of prisoners, and the running of treatment programs, and seems more aimed towards a kind of narrowed organizational skill. The Norwegian prison officer role has been developed close to prison research and with support of unions in a long-term perspective. The Swedish officer role suffers from political-level ad hoc-adjustments to public debate combined with short-termed cost savings inspired by New Public Management ideas.